(R)-2-Amino-3-(3,4-dichlorophenyl)propanoic acid

Base Information

• Chemical Name: (R)-2-Amino-3-(3,4-dichlorophenyl)propanoic acid
• CAS No.: 52794-98-6
• Molecular Formula: C9H9Cl2NO2
• Molecular Weight: 129.93
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID20426364
• Nikkaji Number: J2.638.857K
• Mol file: 52794-98-6.mol

Synonyms:52794-98-6;(R)-2-Amino-3-(3,4-dichlorophenyl)propanoic acid;D-3,4-Dichlorophenylalanine;3,4-Dichloro-D-Phenylalanine;(2R)-2-amino-3-(3,4-dichlorophenyl)propanoic acid;H-D-Phe(3,4-DiCl)-OH;D-3,4-Dichlorophenlalanine;D-Phenylalanine, 3,4-dichloro-;D-3,4-Dichloro phenylalanine;MFCD00671682;H-D-PHE(3,4-CL2)-OH;SCHEMBL289165;DTXSID20426364;AKOS016842342;AC-5851;AM82041;CS-W022745;DS-1298;DS-15309;F12292;D-3,4-Dichlorophenylalanine (H-D-Phe(3,4-diCl)-OH)

Chemical Property of (R)-2-Amino-3-(3,4-dichlorophenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 3.78E-06mmHg at 25°C
• Refractive Index: 1.601
• Boiling Point: 370.6 °C at 760 mmHg
• PKA: 2.14±0.20(Predicted)
• Flash Point: 177.9 °C
• PSA: 63.32000
• Density: 1.45 g/cm³
• LogP: 2.64810
• Storage Temp.: Store at RT.
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 233.0010339
• Heavy Atom Count: 14
• Complexity: 213

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,4-Dichloro-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)Cl)Cl
• Isomeric SMILES: C1=CC(=C(C=C1C[C@H](C(=O)O)N)Cl)Cl
• Uses: 3,4-Dichloro-D-phenylalanine is used in the synthesis of human Pin1 inhibitors. It is also used to prepare morphiceptin analogs with μ-receptor binding activities in brain and mammary adenocarcinoma.

Technology Process of (R)-2-Amino-3-(3,4-dichlorophenyl)propanoic acid

There total 1 articles about (R)-2-Amino-3-(3,4-dichlorophenyl)propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

2-amino-3-(3,4-dichlorophenyl)propionic acid (5472-67-3,52794-99-7) → (R)-2-amino-3-(3,4-dichlorophenyl)propanoic acid (52794-98-6,52794-99-7)

Guidance literature:

With sodium hydroxide; oxygen; 2-amino-2-hydroxymethyl-1,3-propanediol; In water; at 30 ℃; for 22h; pH=7.3; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetlet.2008.08.111

Reference yield: 58.0%

(R)-2-amino-3-(3,4-dichlorophenyl)propanoic acid (52794-98-6,52794-99-7) → (3,4-dichlorophenyl)(5-(3,4-dichlorophenyl)thiazol-2-yl)methanone

Guidance literature:

With sodiumsulfide nonahydrate; water; iodine; acetic acid; In dimethyl sulfoxide; at 100 ℃; for 8h;

DOI:10.1002/adsc.201701130

Reference yield:

(R)-2-amino-3-(3,4-dichlorophenyl)propanoic acid (52794-98-6,52794-99-7) → N-benzylsulfonyl-D-(3,4-dichlorophenyl)alanyl-L-proline (197893-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) aq. NaOH / 1.) dioxane, 2.) dioxane, RT, 2.5 h

2: HOBt, EDC, DIEA / dimethylformamide

3: aq. LiOH / methanol

With lithium hydroxide; sodium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm970493r

upstream raw materials:

2-amino-3-(3,4-dichlorophenyl)propionic acid

Downstream raw materials:

(R)-3-(3,4-Dichloro-phenyl)-2-phenylmethanesulfonylamino-propionic acid

N-benzylsulfonyl-D-(3,4-dichlorophenyl)alanyl-L-proline

(S)-1-[(R)-3-(3,4-Dichloro-phenyl)-2-phenylmethanesulfonylamino-propionyl]-pyrrolidine-2-carboxylic acid methyl ester

Refernces